ethyl 2-(phenylethynyl)-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophene-3-carboxylate | 1384579-41-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 环七噻吩
• 英文名称: ethyl 2-(phenylethynyl)-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophene-3-carboxylate
• CAS: 1384579-41-2
• 化学式: C₂₀H₂₀O₂S
• 分子量: 324.444
• InChiKey: CSVQNGCTFDNBDU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.59
• 重原子数：
  23.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  ethyl 2-(phenylethynyl)-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophene-3-carboxylate 在 碘 、 palladium diacetate 、 potassium carbonate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.17h， 生成 (E)-ethyl-3-(4-oxo-2-phenyl-4H-6,7,8,9-tetrahydro-5H-cyclohepta[4,5]thieno[3,2-c]pyran-4-yl)acrylate
  参考文献：
  名称：

  Thieno[3,2-c]pyran-4-one based novel small molecules: Their synthesis, crystal structure analysis and in vitro evaluation as potential anticancer agents

  摘要：

  Novel thieno[3,2-c]pyran-4-one based small molecules were designed as potential anticancer agents. Expeditious synthesis of these compounds was carried out via a multi-step sequence consisting of few steps such as Gewald reaction, Sandmeyer type iodination, Sonogashira type coupling followed by iodocyclization and then Pd-mediated various C-C bond forming reactions. The overall strategy involved the construction of thiophene ring followed by the fused pyranone moiety and then functionalization at C-7 position of the resultant thieno[3,2-c]pyran-4-one framework. Some of the compounds synthesized showed selective growth inhibition of cancer cells in vitro among which two compounds for example, 5d and 6c showed IC50 values in the range of 2.0-2.5 mu M. The crystal structure analysis of an active compound along with hydrogen bonding patterns and molecular arrangement present within the molecule is described. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.04.109
• 作为产物：
  描述：

  氰乙酸乙酯 在 吗啉 、 copper(l) iodide 、 palladium 10% on activated carbon 、 对甲苯磺酸 、 sulfur 、 三乙胺 、 三苯基膦 、 potassium iodide 、 sodium nitrite 作用下， 以 乙醇 、 水 、 乙腈 为溶剂， 反应 4.33h， 生成 ethyl 2-(phenylethynyl)-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophene-3-carboxylate
  参考文献：
  名称：

  Thieno[3,2-c]pyran-4-one based novel small molecules: Their synthesis, crystal structure analysis and in vitro evaluation as potential anticancer agents

  摘要：

  Novel thieno[3,2-c]pyran-4-one based small molecules were designed as potential anticancer agents. Expeditious synthesis of these compounds was carried out via a multi-step sequence consisting of few steps such as Gewald reaction, Sandmeyer type iodination, Sonogashira type coupling followed by iodocyclization and then Pd-mediated various C-C bond forming reactions. The overall strategy involved the construction of thiophene ring followed by the fused pyranone moiety and then functionalization at C-7 position of the resultant thieno[3,2-c]pyran-4-one framework. Some of the compounds synthesized showed selective growth inhibition of cancer cells in vitro among which two compounds for example, 5d and 6c showed IC50 values in the range of 2.0-2.5 mu M. The crystal structure analysis of an active compound along with hydrogen bonding patterns and molecular arrangement present within the molecule is described. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.04.109